[Question]Trying to Start Seriously on Upwork After 7–8 Years in Software Engineering & AI — Need Real Advice
Hey everyone,
I’m a software engineer with around 7–8 years of experience in web and mobile app development. Over the last couple of years I’ve also moved heavily into AI development — things like AI voice agents, RAG systems, LLM apps, vector databases, automation, OpenAI integrations, etc.
I actually created my Upwork account around 5 years ago, but I never seriously focused on freelancing because I was busy with full-time work and agency projects. Back then I only tested a few proposals just to see how the platform worked. I don’t even remember connects being a big thing at that time.
Now I’m trying to seriously move toward Upwork/freelancing, but honestly it feels very difficult.
Everywhere I read people are saying:
jobs are slower now
competition is extremely high
AI/ChatGPT changed the market
many jobs get 50+ proposals within minutes
As someone starting seriously on Upwork with no reviews, it feels hard to understand how a new profile can realistically compete.
I’d really appreciate real advice from people who actually grew in the last 1–2 years, especially in development/AI.
Some questions I have:
What kind of jobs should a new profile target first?
Is it better to start with small jobs just for reviews?
How important are niche skills vs proposal writing?
Do clients care more about portfolio or Upwork history?
Is boosting proposals worth it?
How do you stand out when 50+ people apply?
I’m not looking for “guru” advice — just real experiences from people who are actually working on Upwork today.
Would appreciate any guidance. Thanks 🙏